Organic electroluminescence device and condensed cyclic compound for organic electroluminescence device

ABSTRACT

An organic electroluminescence device of an embodiment includes a first electrode and a second electrode facing each other, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one organic layer includes a condensed cyclic compound represented by Formula 1, thereby showing improved device efficiency and life.

CROSS-REFERENCE TO RELATED APPLICATIONS

This U.S. non-provisional patent application claims priority under 35U.S.C. § 119 of Korean Patent Application No. 10-2018-0063453, filed onJun. 1, 2018, the entire content of which is hereby incorporated byreference.

BACKGROUND

The present disclosure herein relates to an organic electroluminescencedevice and a condensed cyclic compound used therein.

Recently, the development of an organic electroluminescence displaydevice as an image display device is being actively conducted. Theorganic electroluminescence display device is so-called aself-luminescent display device in which holes and electrons injectedfrom a first electrode and a second electrode recombine in an emissionlayer to produce excitons, and light is generated through the transitionof the excitons thus produced to a ground state to attain display.

In the application of an organic electroluminescence device to a displaydevice, lower driving voltage, higher emission efficiency, and longerlife of the organic electroluminescence device are desired. Hence,materials for an organic electroluminescence device that stably attainthe above desired qualities are being continuously developed.

Meanwhile, in order to achieve an organic electroluminescence devicewith high efficiency, development on a material for a hole transportlayer for restraining the diffusion, etc. of the exciton energy of anemission layer is being conducted.

SUMMARY

The present disclosure provides an organic electroluminescence devicehaving improved emission efficiency and device life.

The present disclosure also provides a condensed cyclic compound whichmay improve the emission efficiency and device life of an organicelectroluminescence device.

An embodiment of the inventive concept provides an organicelectroluminescence device including a first electrode, a secondelectrode disposed on the first electrode, and a plurality of organiclayers disposed between the first electrode and the second electrode,wherein at least one organic layer of the plurality of organic layersincludes a condensed cyclic compound represented by the followingFormula 1:

In Formula 1, each of Ar1, Ar2, and Ar3 is independently a substitutedor unsubstituted aryl group having 6 to 40 carbon atoms for forming aring, or a substituted or unsubstituted heteroaryl group having 2 to 40carbon atoms for forming a ring, where a case where at least one of Ar2or Ar3 is a substituted or unsubstituted carbazole group is excluded, X1to X3 are each independently *-L-NR₁R₂ one of a1 to a3 is 1 and theothers are 0, L is a direct linkage, a substituted or unsubstitutedarylene group having 6 to 30 carbon atoms for forming a ring, or asubstituted or unsubstituted heteroarylene group having 2 to 30 carbonatoms for forming a ring. R₁ and R₂ are each independently a substitutedor unsubstituted alkyl group having 1 to 20 carbon atoms, a substitutedor unsubstituted aryl group having 6 to 40 carbon atoms for forming aring, or a substituted or unsubstituted heteroaryl group having 2 to 40carbon atoms for forming a ring, or combined with each other to form aring.

In an embodiment, the plurality of organic layers may include anemission layer, and a hole transport region disposed between the firstelectrode and the emission layer, and the hole transport region mayinclude the condensed cyclic compound represented by Formula 1.

In an embodiment, the emission layer may emit blue light.

In an embodiment, the emission layer may include at least one ofanthracene derivatives, pyrene derivatives, fluoranthene derivatives,chrysene derivatives, dihydro benzanthracene derivatives, ortriphenylene derivatives.

In an embodiment, Formula 1 may be represented by the following Formula1-1 or Formula 1-2:

In Formula 1-1 and Formula 1-2, Ar1, Ar2, Ar3, L, R₁ and R₂ are the sameas defined in Formula 1.

In an embodiment, Ar1 may be a substituted or unsubstituted benzenering, or a substituted or unsubstituted naphthalene ring.

In an embodiment, Ar2 and Ar3 may be each independently a substituted orunsubstituted benzene ring, a substituted or unsubstituted naphthalenering, a substituted or unsubstituted phenanthrene ring, a substituted orunsubstituted benzofuran ring, a substituted or unsubstituteddibenzofuran ring, a substituted or unsubstituted benzothiophene ring, asubstituted or unsubstituted dibenzothiophene ring, a substituted orunsubstituted pyridine ring, or a substituted or unsubstituted quinolinering.

In an embodiment, Ar2 and Ar3 may be the same.

In an embodiment, Ar2 and Ar3 may be each independently represented byany one of the following Ar-a to Ar-i:

In Ar-a to Ar-i, R₁₁ to R₁₉ are each independently a hydrogen atom, adeuterium atom, a halogen atom, a substituted or unsubstituted silylgroup, a substituted or unsubstituted alkyl group having 1 to 10 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30 carbonatoms for forming a ring, or a substituted or unsubstituted heteroarylgroup having 2 to 30 carbon atoms for forming a ring, or combined withan adjacent group to form a ring, all to a19 are each independently aninteger of 0 to 4, and dotted lines represent combined parts forming acondensed ring.

In an embodiment, Formula 1 may be represented by the following Formula2-1 or Formula 2-2:

In Formula 2-1 and Formula 2-2, each of R₃ and R₄ is independently ahydrogen atom, a deuterium atom, a halogen atom, a substituted orunsubstituted silyl group, a substituted or unsubstituted alkyl grouphaving 1 to 10 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms for forming a ring, or a substituted orunsubstituted heteroaryl group having 2 to 30 carbon atoms for forming aring, or combined with an adjacent group to form a ring, “y” and “z” areeach independently an integer of 0 to 3, and X1 to X3, and a1 to a3 arethe same as defined in Formula 1.

In an embodiment, at least one organic layer includes at least one ofthe compounds represented in the following Compound Group 1 and CompoundGroup 2:

In an embodiment of the inventive concept, a condensed cyclic compoundrepresented by Formula 1 is provided.

The condensed cyclic compound of an embodiment may be used as a materialfor an organic electroluminescence device.

BRIEF DESCRIPTION OF THE FIGURES

The accompanying drawings are included to provide a furtherunderstanding of the inventive concept, and are incorporated in andconstitute a part of this specification. The drawings illustrateexemplary embodiments of the inventive concept and, together with thedescription, serve to explain principles of the inventive concept. Inthe drawings:

FIG. 1 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment of the inventiveconcept;

FIG. 2 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment of the inventiveconcept; and

FIG. 3 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment of the inventiveconcept.

DETAILED DESCRIPTION

The inventive concept may have various modifications and may be embodiedin different forms, and example embodiments will be explained in detailwith reference to the accompanying drawings. The inventive concept may,however, be embodied in different forms and should not be construed aslimited to the embodiments set forth herein. Rather, all modifications,equivalents, and substituents which are included in the spirit andtechnical scope of the inventive concept should be included in theinventive concept.

Like reference numerals refer to like elements throughout. In thedrawings, the dimensions of structures are exaggerated for clarity ofillustration. It will be understood that, although the terms first,second, etc. may be used herein to describe various elements, theseelements should not be limited by these terms. These terms are only usedto distinguish one element from another element. Thus, a first elementcould be termed a second element without departing from the teachings ofthe present invention. Similarly, a second element could be termed afirst element. As used herein, the singular forms are intended toinclude the plural forms as well, unless the context clearly indicatesotherwise.

It will be further understood that the terms “comprises” and/or“comprising,” when used in this specification, specify the presence ofstated features, numerals, steps, operations, elements, parts, or thecombination thereof, but do not preclude the presence or addition of oneor more other features, numerals, steps, operations, elements, parts, orthe combination thereof.

In the description, it will also be understood that when a layer, afilm, a region, a plate, etc. is referred to as being ‘on’ or “above”another part, it can be directly on the other part, or interveninglayers may also be present. On the contrary, when a layer, a film, aregion, a plate, etc. is referred to as being ‘under’ or “below” anotherpart, it can be directly under the other part, or intervening layers mayalso be present. In addition, in the description, the disposition “on”may include the disposition below as well as above.

In the description, the term “substituted or unsubstituted” correspondsto substituted or unsubstituted with at least one substituent selectedfrom the group consisting of a deuterium atom, a halogen atom, a cyanogroup, a nitro group, an amino group, a silyl group, a boron group, aphosphine oxide group, a phosphine sulfide group, an alkyl group, analkenyl group, an alkoxy group, a hydrocarbon ring group, an aryl group,and a heterocyclic group. In addition, each of the substituents may besubstituted or unsubstituted. For example, a biphenyl group may beinterpreted as an aryl group or a phenyl group substituted with a phenylgroup.

In the description, the halogen atom may include a fluorine atom, achlorine atom, a bromine atom and an iodine atom.

In the description, the alkyl may be a linear, branched or cyclic type.The carbon number of the alkyl may be from 1 to 50, from 1 to 30, from 1to 20, from 1 to 10, or from 1 to 6. Examples of the alkyl may includemethyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, i-butyl,2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl,t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl,4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl,cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl,1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl,n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl,3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl,2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl,n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldocecyl,2-octyldodecyl, n-tridecyl, n-tetradecyl, c-pentadecyl, n-hexadecyl,2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl,n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl,2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-henicosyl, n-docosyl,n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl,n-octacosyl, n-nonacosyl, n-triacontyl, etc., without limitation.

In the description, the hydrocarbon ring group means an optionalfunctional group or substituent derived from an aliphatic hydrocarbonring. The hydrocarbon ring group may be a saturated hydrocarbon ringgroup having 5 to 20 carbon atoms for forming a ring.

In the description, the aryl group means an optional functional group orsubstituent derived from an aromatic hydrocarbon ring. The aryl groupmay be a monocyclic aryl group or a polycyclic aryl group. The carbonnumber for forming a ring in the aryl group may be 6 to 30, 6 to 20, or6 to 15. Examples of the aryl group may include phenyl, naphthyl,fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl,quinqphenyl, sexiphenyl, triphenylenyl, pyrenyl, benzofluoranthenyl,chrysenyl, etc., without limitation.

In the description, the fluorenyl group may be substituted, and twosubstituents may be combined with each other to form a spiro structure.Examples of substituted fluorenyl groups are as follows. However, anembodiment of the inventive concept is not limited thereto.

In the description, the heteroaryl may include one or more of B, O, N,P, Si and S as heteroatoms. If the heteroaryl group includes two or moreheteroatoms, two or more heteroatoms may be the same or different. Theheteroaryl group may be a monocyclic heterocycle or a polycyclicheterocycle. The carbon number for forming a ring of the heteroaryl maybe 2 to 30, 2 to 20, or 2 to 10. Examples of the heteroaryl may includethiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole,triazole, pyridine, bipyridine, pyrimidine, triazine, triazole, acridyl,pyridazine, pyrazinyl, quinoline, quinazoline, quinoxaline, phenoxazine,phthalazine, pyrido pyrimidine, pyrido pyrazine, pyrazino pyrazine,isoquinoline, indole, carbazole, N-arylcarbazole, N-heteroarylcarbazole,N-alkylcarbazole, benzoxazole, benzoimidazole, benzothiazole,benzocarbazole, benzothiophene, dibenzothiophene, thienothiophene,benzofuran, phenanthroline, thiazole, isooxazole, oxadiazole,thiadiazole, phenothiazine, dibenzosilole, dibenzofuran, etc., withoutlimitation.

In the description, the silyl group includes an alkyl silyl group and anaryl silyl group. Examples of the silyl group may includetrimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl,prop yldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.However, an embodiment of the inventive concept is not limited thereto.

In the description, the carbon number of the amino group is notspecially limited, but may be 1 to 30. The amino group may include analkyl amino group, an aryl amino group, or a heteroaryl amino group.Examples of the amino group may be a methylamino group, a dimethylaminogroup, a phenylamino group, a diphenylamino group, a naphthylaminogroup, a 9-methyl-anthracenylamino group, a triphenylamino group, etc.However, an embodiment of the inventive concept is not limited thereto.

Meanwhile, in the description, “*-” means a connecting position, and adotted line (

) means a connecting part to form a condensed ring.

Hereinafter, an organic electroluminescence device according to anembodiment of the inventive concept and a condensed cyclic compound ofan embodiment included therein will be explained with reference toattached drawings.

FIG. 1, FIG. 2, and FIG. 3 are cross-sectional views schematicallyillustrating organic electroluminescence devices according to exemplaryembodiments. Referring to FIG. 1, FIG. 2, and FIG. 3, an organicelectroluminescence device 10 according to an embodiment may include afirst electrode EL1, a hole transport region HTR, an emission layer EML,an electron transport region ETR, and a second electrode EL2 laminatedin that order.

The first electrode EL1 and the second electrode EL2 are oppositelydisposed to each other, and a plurality of organic layers may bedisposed between the first electrode EL1 and the second electrode EL2.The plurality of the organic layers may include the hole transportregion HTR, the emission layer EML, and the electron transport regionETR.

The organic electroluminescence device 10 of an embodiment may includethe condensed cyclic compound of an embodiment, which will be explainedlater, in at least one organic layer of the plurality of organic layersdisposed between the first electrode EL1 and the second electrode EL2.Particularly, the condensed cyclic compound of an embodiment may beincluded in the hole transport region HTR.

When compared with FIG. 1, FIG. 2 shows a cross-sectional view of anorganic electroluminescence device 10 of an embodiment, wherein a holetransport region HTR includes a hole injection layer HIL and a holetransport layer HTL, and an electron transport region ETR includes anelectron injection layer EIL and an electron transport layer ETL. Inaddition, when compared with FIG. 1, FIG. 3 shows a cross-sectional viewof an organic electroluminescence device 10 of an embodiment, wherein ahole transport region HTR includes a hole injection layer HIL, a holetransport layer HTL, and an electron blocking layer EBL, and an electrontransport region ETR includes an electron injection layer EIL, anelectron transport layer ETL, and a hole blocking layer HBL. Meanwhile,in the organic electroluminescence device 10 of an embodiment, the holetransport layer HTL may include the condensed cyclic compound of anembodiment, which will be explained later.

The first electrode EL1 has conductivity. The first electrode EL1 may beformed using a metal alloy or a conductive compound. The first electrodeEL1 may be an anode. In addition, the first electrode EL1 may be a pixelelectrode. The first electrode EL1 may be a transmissive electrode, atransflective electrode, or a reflective electrode. If the firstelectrode EL1 is the transmissive electrode, the first electrode EL1 maybe formed using a transparent metal oxide such as indium tin oxide(ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and indium tin zincoxide (ITZO). If the first electrode EL1 is the transflective electrodeor the reflective electrode, the first electrode EL1 may include Ag, Mg,Cu, Al, Pt, Pd, Au, Ni, Nd, Jr, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, acompound thereof, or a mixture thereof (for example, a mixture of Ag andMg). Also, the first electrode EL1 may have a structure of a pluralityof layers including a reflective layer or a transflective layer formedusing the above materials, and a transmissive conductive layer formedusing ITO, IZO, ZnO, or ITZO. For example, the first electrode EL1 mayinclude a triple layer structure of ITO/Ag/ITO. The thickness of thefirst electrode EL1 may be from about 1,000 Å to about 10,000 Å, forexample, from about 1,000 Å to about 3,000 Å. However, an embodiment ofthe inventive concept is not limited thereto.

The hole transport region HTR is provided on the first electrode ELL Thehole transport region HTR may include at least one of a hole injectionlayer HIL, a hole transport layer HTL, a hole buffer layer (not shown),or an electron blocking layer EBL. The thickness of the hole transportregion HTR may be, for example, from about 1,000 Å to about 1,500 Å.

The hole transport region HTR may have a single layer formed using asingle material, a single layer formed using a plurality of differentmaterials, or a multilayer structure including a plurality of layersformed using a plurality of different materials.

For example, the hole transport region HTR may have a single layerstructure such as a hole injection layer HIL, or a hole transport layerHTL, and may have a single layer structure formed using a hole injectionmaterial and a hole transport material. Alternatively, the holetransport region HTR may have a single layer structure formed using aplurality of different materials, or a structure laminated on the firstelectrode EL1 of hole injection layer HIL/hole transport layer HTL, holeinjection layer HIL/hole transport layer HTL/hole buffer layer (notshown), hole injection layer HIL/hole buffer layer (not shown), holetransport layer HTL/hole buffer layer, or hole injection layer HIL/holetransport layer HTL/electron blocking layer EBL, without limitation.

The hole transport region HTR may be formed using various methods suchas a vacuum deposition method, a spin coating method, a cast method, aLangmuir-Blodgett (LB) method, an inkjet printing method, a laserprinting method, and a laser induced thermal imaging (LITI) method.

The hole transport region HTR may include the condensed cyclic compoundof an embodiment, represented by the following Formula 1:

In Formula 1, Ar1 to Ar3 are each independently a substituted orunsubstituted aryl group having 6 to 40 carbon atoms for forming a ring,or a substituted or unsubstituted heteroaryl group having 2 to 40 carbonatoms for forming a ring, with the exception of a case where at leastone of Ar2 and Ar3 is a carbazole group.

In Formula 1, X1, X2, and X3 may be each independently *-L-NR₁R₂. Inaddition, one of a1 to a3 may be 1, and the others may be 0. That is,*-L-NR₁R₂ may be combined with any one of Ar1 to Ar3.

Accordingly, the condensed ring compound represented by Formula 1 may bea monoamine compound of which core part is substituted with one aminegroup.

In *-L-NR₁R₂, L may be a direct linkage, a substituted or unsubstitutedarylene group having 6 to 30 carbon atoms for forming a ring, or asubstituted or unsubstituted heteroarylene group having 2 to 30 carbonatoms for forming a ring. In addition, in *-L-NR₁R₂, R₁ and R₂ may beeach independently a substituted or unsubstituted alkyl group having 1to 20 carbon atoms, a substituted or unsubstituted aryl group having 6to 40 carbon atoms for forming a ring, or a substituted or unsubstitutedheteroaryl group having 2 to 40 carbon atoms for forming a ring, orcombined with each other to form a ring.

In the condensed ring compound represented by Formula 1, Ar1 may be asubstituted or unsubstituted aryl group having 6 to 40 carbon atoms forforming a ring, or a substituted or unsubstituted heteroaryl grouphaving 2 to 40 carbon atoms for forming a ring, which is condensed to acore part,

For example, Ar1 may be a substituted or unsubstituted aryl group having6 to 18 carbon atoms for forming a ring. Particularly, Ar1 may be asubstituted or unsubstituted benzene ring, or a substituted orunsubstituted naphthalene ring.

In the condensed cyclic compound represented by Formula 1, each of Ar2and Ar3 may be a substituted or unsubstituted aryl group having 6 to 40carbon atoms for forming a ring, or a substituted or unsubstitutedheteroaryl group having 2 to 40 carbon atoms for forming a ring, whichis condensed to a core part,

For example, each of Ar2 and Ar3 may be a substituted or unsubstitutedaryl group having 6 to 18 carbon atoms for forming a ring, or asubstituted or unsubstituted heteroaryl group having 2 to 18 carbonatoms for forming a ring. If Ar2 and Ar3 are each independently asubstituted or unsubstituted heteroaryl group, at least one of N, O or Smay be included as a heteroatom.

However, a case where at least one of Ar2 or Ar3 is a substituted orunsubstituted carbazole group is excluded. That is, cases where thecondensed cyclic part in Formula 1 is represented by E1 to E3 areexcluded.

Meanwhile, each of Ar2 and Ar3 may be independently a substituted orunsubstituted benzene ring, a substituted or unsubstituted naphthalenering, a substituted or unsubstituted phenanthrene ring, a substituted orunsubstituted benzofuran ring, a substituted or unsubstituteddibenzofuran ring, a substituted or unsubstituted benzothiophene ring, asubstituted or unsubstituted dibenzothiophene ring, a substituted orunsubstituted pyridine ring, or a substituted or unsubstituted quinolinering. Particularly, Ar2 and Ar3 may be each independently anunsubstituted benzene ring, an unsubstituted naphthalene ring, anunsubstituted phenanthrene ring, an unsubstituted benzofuran ring, anunsubstituted dibenzofuran ring, an unsubstituted benzothiophene ring,an unsubstituted dibenzothiophene ring, an unsubstituted pyridine ring,or an unsubstituted quinoline ring.

Ar2 and Ar3 may be each independently represented by any one among Ar-ato Ar-i.

In Ar-a to Ar-i, each one of R₁₁ to R₁₉ may be independently a hydrogenatom, a deuterium atom, a halogen atom, a substituted or unsubstitutedsilyl group, a substituted or unsubstituted alkyl group having 1 to 10carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms for forming a ring, or a substituted or unsubstitutedheteroaryl group having 2 to 30 carbon atoms for forming a ring, orcombined with an adjacent group to form a ring. In Ar-a to Ar-i, all toa19 may be each independently an integer of 0 to 4.

Meanwhile, Ar2 and Ar3 may be the same. In an embodiment, Ar2 and Ar3may be the same aryl group or the same heteroaryl group.

Alternatively, Ar2 and Ar3 may be different from each other in anembodiment. For example, Ar2 and Ar3 may be different aryl groups, oneamong Ar2 and Ar3 may be an aryl group and the other one may be aheteroaryl group, or Ar2 and Ar3 may be different heteroaryl groups.

The condensed cyclic compound of an embodiment, represented by Formula1, may have a condensed ring in which at least six rings are condensedby combining the cyclic groups of Ar1 to Ar3 in a core part,

The condensed ring compound of an embodiment includes a condensed ringobtained by condensing at least six rings in a core part, and may haveimproved thermal stability and electron tolerance.

In the condensed ring of an embodiment, represented by Formula 1,*-L-NR₁R₂ group is connected with any one among Ar1 to Ar3, and L is alinker connecting an amine group (NR₁R₂) with a core part and may be adirect linkage or any one represented by the following L1 to L4:

Meanwhile, R₁ and R₂ may be each independently a substituted orunsubstituted phenyl group, a substituted or unsubstituted biphenylgroup, a substituted or unsubstituted naphthyl group, a substituted orunsubstituted terphenyl group, a substituted or unsubstituteddibenzothiophene group, a substituted or unsubstituted dibenzofurangroup, a substituted or unsubstituted carbazole group, a substituted orunsubstituted phenanthryl group, or a substituted or unsubstitutedfluorenyl group.

R₁ and R₂ may be the same or different.

In addition, R₁ and R₂ may be combined with each other to form a ring.For example, R₁ and R₂ may be combined with each other to form any onering among S1 to S3. In S1 to S3, a “*-” part may be a part combinedwith a linker, L.

Meanwhile, each of R₅ and R₆ in S2 may be independently a hydrogen atom,a deuterium atom, a halogen atom, a substituted or unsubstituted silylgroup, a substituted or unsubstituted alkyl group having 1 to 10 carbonatoms, or a substituted or unsubstituted aryl group having 6 to 30carbon atoms for forming a ring.

The condensed cyclic compound represented by Formula 1 may berepresented by the following Formula 1-1 or Formula 1-2:

Formula 1-1 represents a case where an amine group, a *-L-NR₁R₂ part, iscombined with Ar1, Formula 1-2 represents a case where an amine group, a*-L-NR₁R₂ part, is combined with Ar3. Meanwhile, although not shown, the*-L-NR₁R₂ part may be combined with Ar2.

Meanwhile, the same explanation on Formula 1 may be applied to Formula1-1 and Formula 1-2, and the explanation on Art to Ar3, L, R₁ and R₂ maybe applied to Ar1 to Ar3, L, R₁ and R₂ in Formula 1-1 and Formula 1-2.

The condensed cyclic compound of an embodiment, represented by Formula 1may be represented by the following Formula 2-1 or Formula 2-2:

Formula 2-1 represents a case where Ar1 is a substituted orunsubstituted benzene ring in Formula 1, and Formula 2-2 represents acase where Ar1 is a substituted or unsubstituted naphthalene ring inFormula 1.

In Formula 2-1 and Formula 2-2, each of R₃ and R₄ may be independently ahydrogen atom, a deuterium atom, a halogen atom, a substituted orunsubstituted silyl group, a substituted or unsubstituted alkyl grouphaving 1 to 10 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms for forming a ring, or a substituted orunsubstituted heteroaryl group having 2 to 30 carbon atoms for forming aring, or combined with an adjacent group to form a ring.

In Formula 2-1 and Formula 2-2, “y” and “z” may be each independently aninteger of 0 to 3. In “y” or “z” is an integer of 2 or more, a pluralityof R3 or a plurality of R4 may be the same or at least one thereof maybe different.

The organic electroluminescence device 10 of an embodiment as shown inFIGS. 1 to 3 may include at least one of the condensed cyclic compoundsrepresented in Compound Group 1 or Compound Group 2 below in at leastone organic layer disposed between the first electrode EL1 and thesecond electrode EL2. For example, in the hole transport region HTR ofthe organic electroluminescence device 10 of an embodiment, at least oneof the condensed cyclic compounds represented in Compound Group 1 orCompound Group 2 below may be included, particularly, a hole transportlayer HTL may include at least one of the condensed cyclic compoundsrepresented in Compound Group 1 or Compound Group 2 below.

In the compounds shown in Compound Group 1 and Compound Group 2, SiPh₃represents a phenyl substituted silyl group, particularly,triphenylsilyl group.

The condensed cyclic compound represented by Formula 1 includes acondensed ring obtained by condensing six or more rings in a cores part,and one amine group is substituted for the condensed ring, therebyshowing excellent hole transport properties and improved thermalstability and electron tolerance.

In the organic electroluminescence device 10 of an embodiment, as shownin FIGS. 1 to 3, a hole transport region HTR may include one kind, twoor more kinds of the condensed cyclic compounds in Compound Group 1 andCompound Group 2. Meanwhile, the hole transport region HTR may furtherinclude a known material in addition to the condensed compounds inCompound Group 1 or Compound Group 2.

The organic electroluminescence device 10 of an embodiment includes thecondensed cyclic compound of an embodiment in a hole transport regionHTR, and may further include a known hole injection material or a knownhole transport material in a hole transport region HTR, or at least oneof a hole injection layer HIL or a hole transport layer HTL.

The hole injection layer HIL may include, for example, a phthalocyaninecompound such as copper phthalocyanine;N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine(DNTPD), 4,4′,4″-tris(3-methylphenylphenylamino) triphenylamine(m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA),4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate)(PANI/PSS), N,N′-di(naphthalene-1-yl)-N,N′-diphenyl)-benzidine (NPB),triphenylamine-containing polyether ketone (TPAPEK),4-isopropyl-4′-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate,dipyrazino[2,3-f: 2′,3′-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile(HAT-CN), etc.

The hole transport layer HTL may include in addition to the condensedcyclic compound of an embodiment, for example, carbazole derivativessuch as N-phenyl carbazole and polyvinyl carbazole, fluorine-basedderivatives,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), triphenylamine-based derivatives such as4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),N,N′-di(naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPB),4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC),4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD),1,3-bis(N-carbazolyl)benzene (mCP), etc.

The thickness of the hole transport region HTR may be from about 100 Åto about 10,000 Å, for example, from about 100 Å to about 5,000 Å. Thethickness of the hole injection layer HIL may be, for example, fromabout 30 Å to about 1,000 Å, and the thickness of the hole transportlayer HTL may be from about 30 Å to about 1,000 Å. For example, thethickness of the electron blocking layer EBL may be from about 10 Å toabout 1,000 Å. If the thicknesses of the hole transport region HTR, thehole injection layer HIL, the hole transport layer HTL and the electronblocking layer EBL satisfy the above-described ranges, satisfactory holetransport properties may be achieved without substantial increase of adriving voltage.

The hole transport region HTR may further include a charge generatingmaterial in addition to the above-described materials to increaseconductivity. The charge generating material may be dispersed uniformlyor non-uniformly in the hole transport region HTR. The charge generatingmaterial may be, for example, a p-dopant. The p-dopant may be one ofquinone derivatives, metal oxides, or cyano group-containing compounds,without limitation. For example, non-limiting examples of the p-dopantmay include quinone derivatives such as tetracyanoquinodimethane (TCNQ)and 2,3,5,6,7,7,8,8-tetrafluoro-tetracyanoquinodimethane (F4-TCNQ),metal oxides such as tungsten oxide, and molybdenum oxide, withoutlimitation.

As described above, the hole transport region HTR may further include atleast one of a hole buffer layer (not shown) or an electron blockinglayer EBL in addition to the hole injection layer HIL and the holetransport layer HTL. The hole buffer layer (not shown) may compensate anoptical resonance distance according to the wavelength of light emittedfrom an emission layer EML and may increase light-emitting efficiency.Materials which may be included in the hole transport region HTR may beused as materials which may be included in the hole buffer layer (notshown). The electron blocking layer EBL is a layer which plays the roleof preventing electron injection from the electron transport region ETRto the hole transport region HTR.

The emission layer EML is provided on the hole transport region HTR. Thethickness of the emission layer EML may be, for example, from about 100Å to about 1,000 Å, or from about 100 Å to about 300 Å. The emissionlayer EML may have a single layer formed using a single material, asingle layer formed using a plurality of different materials, or amultilayer structure having a plurality of layers formed using aplurality of different materials.

The emission layer EML in the organic electroluminescence device 10 ofan embodiment may include anthracene derivatives, pyrene derivatives,fluoranthene derivatives, chrysene derivatives, dihydro benzanthracenederivatives, or triphenylene derivatives. Particularly, the emissionlayer EML may include anthracene derivatives or pyrene derivatives.

The emission layer EML may include anthracene derivatives represented bythe following Formula 3:

In Formula 3, R₃₁ to R₄₀ are each independently a hydrogen atom, adeuterium atom, a halogen atom, a substituted or unsubstituted silylgroup, a substituted or unsubstituted alkyl group having 1 to 10 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30 carbonatoms for forming a ring, or a substituted or unsubstituted heteroarylgroup having 2 to 30 carbon atoms for forming a ring, or may be combinedwith an adjacent group to form a ring. Meanwhile, R₃₁ to R₄₀ may becombined with an adjacent group to form a saturated hydrocarbon ring oran unsaturated hydrocarbon ring.

In Formula 3, each of “c” and “d” may be independently an integer of 0to 5.

Formula 3 may be represented by any one of the following Formula 3-1 toFormula 3-6:

In the organic electroluminescence device 10 of an embodiment as shownin FIGS. 1 to 3, the emission layer EML may include a host and a dopant,and the emission layer EML may include the compound represented byFormula 3 as a host material.

The emission layer EML may be a blue emission layer which emits bluelight having a wavelength region of less than about 470 nm. For example,the emission layer EML may be a layer emitting deep blue light which hasa wavelength region of about 440 nm to about 470 nm, or about 450 nm toabout 470 nm.

The emission layer EML may further include a common material known inthe art as a host material. For example, the emission layer EML mayinclude as the host material at least one ofbis[2-(diphenylphosphino)phenyl] ether oxide (DPEPO),4,4′-bis(carbazol-9-yl)biphenyl (CBP), 1,3-bis(N-carbazolyl)benzene(mCP), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF),4,4′,4″-tris(carbazol-9-yl)-triphenylamine (TcTa) or1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBi). However, anembodiment of the inventive concept is not limited thereto. For example,tris(8-hydroxyquinolino)aluminum (Alq₃), 4poly(N-vinylcarbazole) (PVK),9,10-di(naphthalene-2-yl)anthracene (ADN),4,4′,4″-tris(carbazol-9-yl)-triphenylamine (TCTA),1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBi),3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), distyrylarylene(DSA), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),bis[2-(diphenylphosphino)phenyl] ether oxide (DPEPO), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2),hexaphenylcyclotrisiloxane (DPSiO₃), octaphenylcyclotetrasiloxane(DPSiO₄), 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF), etc., may beused as the host material.

In an embodiment, the emission layer EML may include as a known dopantmaterial, styryl derivatives (for example,1,4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene (BCzVB),4-(di-p-tolylamino)-4′-[(di-p-tolylamino)styryl]stilbene (DPAVB), andN-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine(N-BDAVBi), perylene and the derivatives thereof (for example,2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and the derivativesthereof (for example, 1,1-dipyrene, 1,4-dipyrenylbenzene,1,4-bis(N,N-diphenylamino)pyrene), etc.

In the organic electroluminescence device 10 of an embodiment, as shownin FIGS. 1 to 3, the electron transport region ETR is provided on theemission layer EML. The electron transport region ETR may include atleast one of a hole blocking layer HBL, an electron transport layer ETLor an electron injection layer EIL. However, an embodiment of theinventive concept is not limited thereto.

The electron transport region ETR may have a single layer formed using asingle material, a single layer formed using a plurality of differentmaterials, or a multilayer structure having a plurality of layers formedusing a plurality of different materials.

For example, the electron transport region ETR may have a single layerstructure of an electron injection layer EIL or an electron transportlayer ETL, or a single layer structure formed using an electroninjection material and an electron transport material. Further, theelectron transport region ETR may have a single layer structure having aplurality of different materials, or a structure laminated from theemission layer EML of electron transport layer ETL/electron injectionlayer EIL, or hole blocking layer HBL/electron transport layerETL/electron injection layer EIL, without limitation. The thickness ofthe electron transport region ETR may be, for example, from about 1,000Å to about 1,500 Å.

The electron transport region ETR may be formed using various methodssuch as a vacuum deposition method, a spin coating method, a castmethod, a Langmuir-Blodgett (LB) method, an inkjet printing method, alaser printing method, and a laser induced thermal imaging (LITI)method.

If the electron transport region ETR includes an electron transportlayer ETL, the electron transport region ETR may include ananthracene-based compound. For example, the electron transport layer mayinclude tris(8-hydroxyquinolinato)aluminum (Alq3),1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene,2,4,6-tris(3′-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine,2-(4-(N-phenylbenzoimidazolyl-1-ylphenyl)-9,10-dinaphthylanthracene,1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi),2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen),3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ),4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ),2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD),bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum(BAlq), berylliumbis(benzoquinolin-10-olate (Bebq₂),9,10-di(naphthalene-2-yl)anthracene (ADN), or a mixture thereof, withoutlimitation. The thickness of the electron transport layer ETL may befrom about 100 Å to about 1,000 Å and may be, for example, from about150 Å to about 500 Å. If the thickness of the electron transport layerETL satisfies the above-described range, satisfactory electron transportproperties may be obtained without substantial increase of a drivingvoltage.

If the electron transport region ETR includes the electron injectionlayer EIL, the electron transport region ETR may include, for example,LiF, lithium quinolate (LiQ), Li₂O, BaO, NaCl, CsF, a metal inlanthanoides such as Yb, or a metal halide such as RbCl and RbI.However, an embodiment of the inventive concept is not limited thereto.The electron injection layer EIL may also be formed using a mixturematerial of an electron transport material and an insulating organometal salt. The organo metal salt may be a material having an energyband gap of about 4 eV or more. Particularly, the organo metal salt mayinclude, for example, metal acetates, metal benzoates, metalacetoacetates, metal acetylacetonates, or metal stearates. The thicknessof the electron injection layer EIL may be from about 1 Å to about 100Å, and from about 3 Å to about 90 Å. If the thickness of the electroninjection layer EIL satisfies the above described range, satisfactoryelectron injection properties may be obtained without inducingsubstantial increase of a driving voltage.

The electron transport region ETR may include a hole blocking layer HBLas described above. The hole blocking layer HBL may include, forexample, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline(BCP), or 4,7-diphenyl-1,10-phenanthroline (Bphen). However, anembodiment of the inventive concept is not limited thereto.

The second electrode EL2 is provided on the electron transport regionETR. The second electrode EL2 may be a common electrode or a cathode.The second electrode EL2 may be a transmissive electrode, atransflective electrode or a reflective electrode. If the secondelectrode EL2 is the transmissive electrode, the second electrode EL2may include a transparent metal oxide, for example, ITO, IZO, ZnO, ITZO,etc.

If the second electrode EL2 is the transflective electrode or thereflective electrode, the second electrode EL2 may include Ag, Mg, Cu,Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, acompound or a mixture including thereof (for example, a mixture of Agand Mg). The second electrode EL2 may have a multilayered structureincluding a reflective layer or a transflective layer formed using theabove-described materials and a transparent conductive layer formedusing ITO, IZO, ZnO, ITZO, etc.

Although not shown, the second electrode EL2 may be connected with anauxiliary electrode. If the second electrode EL2 is connected with theauxiliary electrode, the resistance of the second electrode EL2 maydecrease.

Meanwhile, although not shown in the drawings, on the second electrodeEL2 of the organic electroluminescence device 10 of an embodiment, acapping layer (not shown) may be further disposed. The capping layer(not shown) may include, for example, α-NPD, NPB, TPD, m-MTDATA, Alq3,CuPc, N4,N4,N4′,N4′-tetra(biphenyl-4-yl) biphenyl-4,4′-diamine (TPD15),4,4′,4″-tris(carbazol sol-9-yl) triphenylamine (TCTA),N,N′-bis(naphthalen-1-yl), etc.

In the organic electroluminescence device 10, according to theapplication of a voltage to each of the first electrode EL1 and secondelectrode EL2, holes injected from the first electrode EL1 may move viathe hole transport region HTR to the emission layer EML, and electronsinjected from the second electrode EL2 may move via the electrontransport region ETR to the emission layer EML. The electrons and theholes are recombined in the emission layer EML to produce excitons, andthe excitons may emit light via transition from an excited state to aground state.

The condensed cyclic compound may be used as a material for an organicelectroluminescence device 10. The organic electroluminescence device 10according to an embodiment of the inventive concept may include thecondensed cyclic compound in at least one organic layer disposed betweena first electrode EL1 and a second electrode EL2, or a capping layer(not shown) disposed on the second electrode EL2.

Particularly, the organic electroluminescence device 10 according to anembodiment of the inventive concept includes the condensed cycliccompound in at least one organic layer disposed between the firstelectrode EL1 and the second electrode EL2 and may show improvedemission efficiency and life characteristic. Particularly, the organicelectroluminescence device 10 according to an embodiment includes thecondensed cyclic compound in a hole transport region HTR, therebyshowing improved emission efficiency and life characteristic and lowdriving property.

Hereinafter, a condensed cyclic compound according to an embodiment ofthe inventive concept and an organic electroluminescence device of anembodiment will be explained in more detail with reference toembodiments and comparative embodiments. The following embodiments areonly illustrations to assist the understanding of the inventive concept,and the scope of the inventive concept is not limited thereto

EXAMPLES 1. Synthesis of Condensed Cyclic Compounds

First, the synthetic method of the condensed cyclic compound accordingto an embodiment of the inventive concept will be particularly explainedreferring to the synthetic methods of Compound A8, Compound A48,Compound A57, Compound A59, Compound B40 and Compound B53. In addition,the synthetic methods of the condensed cyclic compounds explained beloware only examples, and the synthetic method of a condensed cycliccompound according to an embodiment of the inventive concept is notlimited thereto.

(1) Synthesis of Compound A8

A condensed cyclic compound according to an embodiment, Compound A8, maybe synthesized, for example, by the following Reaction 1:

<Synthesis of Intermediate IM-1>

Under an argon (Ar) atmosphere, to a 500 ml, three neck flask, 20.00 g(170.7 mmol) of indole, 12.78 g (0.1 equiv, 56.9 mmol) of Pd(OAc)₂,157.30 g (2 equiv, 1.13 mol) of K₂CO₃, 51.01 g (1.2 equiv, 204.9 mmol)of 2-iodo-1-nitrobenzene and 341 ml of 1,4-dioxane were added in thatorder, followed by heating, stirring and refluxing for about 24 hours.After cooling to room temperature, the reaction product was filteredwith celite to separate insoluble residue, water was added, and anorganic layer was separately taken. To an aqueous layer, toluene wasadded, and an organic layer was extracted once more. The organic layerthus collected was washed with a saline solution and dried with MgSO₄.MgSO₄ was separated, and the organic layer was concentrated and then,the crude product thus obtained was separated by silica gel columnchromatography (using a mixture solvent of hexane and toluene as adeveloper) to obtain Intermediate IM-1 (17.08 g, yield 42%) as a whitesolid compound. A molecular ion peak of m/z=238 was observed bymeasuring FAB-MS, and from the result, the product was identified asIntermediate IM-1.

<Synthesis of Intermediate IM-2>

Under an argon atmosphere, to a 300 ml, three-neck flask, 15.00 g (63.0mmol) of IM-1, 126 ml of o-dichlorobenzene and 41.85 g (4 equiv, 251.8mmol) of P(OEt)₃ were added in that order, followed by heating andstirring at about 160° C. for about 24 hours. After cooling to roomtemperature, the reaction solvents were distilled off, and the crudeproduct thus obtained was separated by silica gel column chromatography(using a mixture solvent of hexane and toluene as a developer) to obtainIntermediate IM-2 (10.39 g, yield 80%) as a white solid compound. Amolecular ion peak of m/z=206 was observed by measuring FAB-MS, and fromthe result, the product was identified as Intermediate IM-2.

<Synthesis of Intermediate IM-3>

Under an argon atmosphere, to a 500 ml, three neck flask, 10.00 g (48.5mmol) of Intermediate IM-2, 0.84 g (0.03 equiv, 1.5 mmol) of Pd(dba)₂,11.65 g (2.5 equiv, 121.2 mmol) of NaOtBu, 242 ml of toluene, 13.11 g (1equiv, 48.5 mmol) of 1,2-dibromo-3-chlorobenzene and 0.98 g (0.1 equiv,4.8 mmol) of tBu3P were added in that order, followed by heating,stirring and refluxing for about 6 hours. After cooling to roomtemperature, water was added to the reaction product, and an organiclayer was separately taken. To an aqueous layer, toluene was added, andan organic layer was extracted once more. The organic layer thuscollected was washed with a saline solution and dried with MgSO₄. MgSO₄was separated, and the organic layer was concentrated and then, thecrude product thus obtained was separated by silica gel columnchromatography (using a mixture solvent of hexane and toluene as adeveloper) to obtain Intermediate IM-3 (11.45 g, yield 75%) as a whitesolid compound. A molecular ion peak of m/z=314 was observed bymeasuring FAB-MS, and from the result, the product was identified asIntermediate IM-3.

<Synthesis of Compound A8>

Under an argon atmosphere, to a 500 ml, three neck flask, 5.00 g (15.9mmol) of Intermediate IM-3, 0.27 g (0.03 equiv, 0.5 mmol) of Pd(dba)₂,3.05 g (2 equiv, 31.8 mmol) of NaOtBu, 80 ml of toluene, 5.62 g (1.1equiv, 17.5 mmol) of bis(4-biphenyl)amine and 0.32 g (0.1 equiv, 1.6mmol) of tBu3P were added in that order, followed by heating, stirringand refluxing for about 6 hours. After cooling to room temperature,water was added to the reaction product, and an organic layer wasseparately taken. To an aqueous layer, toluene was added, and an organiclayer was extracted once more. The organic layer thus collected waswashed with a saline solution and dried with MgSO₄. MgSO₄ was separated,and the organic layer was concentrated and then, the crude product thusobtained was separated by silica gel column chromatography (using amixture solvent of hexane and toluene as a developer) to obtain CompoundA8 (7.62 g, yield 80%) as a white solid compound. A molecular ion peakof m/z=599 was observed by measuring FAB-MS, and from the result, theproduct was identified as Compound A8.

(2) Synthesis of Compound A48

A condensed cyclic compound according to an embodiment, Compound A48,may be synthesized, for example, by the following Reaction 2:

<Synthesis of Intermediate IM-4>

Under an argon atmosphere, to a 500 ml, three neck flask, 10.00 g (48.5mmol) of Intermediate IM-2, 0.84 g (0.03 equiv, 1.5 mmol) of Pd(dba)₂,11.65 g (2.5 equiv, 121.2 mmol) of NaOtBu, 242 ml of toluene, 13.11 g (1equiv, 48.5 mmol) of 1,2-dibromo-3-chlorobenzene and 0.98 g (0.1 equiv,4.8 mmol) of tBu3P were added in that order, followed by heating,stirring and refluxing for about 6 hours. After cooling to roomtemperature, water was added to the reaction product, and an organiclayer was separately taken. To an aqueous layer, toluene was added, andan organic layer was extracted once more. The organic layer thuscollected was washed with a saline solution and dried with MgSO₄. MgSO₄was separated, and the organic layer was concentrated and then, thecrude product thus obtained was separated by silica gel columnchromatography (using a mixture solvent of hexane and toluene as adeveloper) to obtain Intermediate IM-4 (11.14 g, yield 73%) as a whitesolid compound. A molecular ion peak of m/z=314 was observed bymeasuring FAB-MS, and from the result, the product was identified asIntermediate IM-4.

<Synthesis of Compound A48>

Under an argon atmosphere, to a 500 ml, three neck flask, 5.00 g (15.9mmol) of Intermediate IM-4, 0.27 g (0.03 equiv, 0.5 mmol) of Pd(dba)₂,3.05 g (2 equiv, 31.8 mmol) of NaOtBu, 80 ml of toluene, 6.50 g (1.1equiv, 17.5 mmol) of bis(4-(naphthalen-1-yl)phenyl)amine and 0.32 g (0.1equiv, 1.6 mmol) of tBu3P were added in that order, followed by heating,stirring and refluxing for about 6 hours. After cooling to roomtemperature, water was added to the reaction product, and an organiclayer was separately taken. To an aqueous layer, toluene was added, andan organic layer was extracted once more. The organic layer thuscollected was washed with a saline solution and dried with MgSO₄. MgSO₄was separated, and the organic layer was concentrated and then, thecrude product thus obtained was separated by silica gel columnchromatography (using a mixture solvent of hexane and toluene as adeveloper) to obtain Compound A48 (8.77 g, yield 85%) as a white solidcompound. A molecular ion peak of m/z=649 was observed by measuringFAB-MS, and from the result, the product was identified as Compound A48.

(3) Synthesis of Compound A57

A condensed cyclic compound according to an embodiment, Compound A57,may be synthesized, for example, by the following Reaction 3:

Under an argon atmosphere, to a 300 ml, three neck flask, 5.00 g (15.9mmol) of Intermediate IM-4, 9.15 g (1.1 equiv, 17.5 mmol) ofN,N-di(4-biphenylyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline,6.59 g (3 equiv, 47.7 mmol) of K₂CO₃, 0.92 g (0.05 equiv, 0.8 mmol) ofPd(PPh₃)₄, and 110 ml of a mixture solution of toluene/ethanol(EtOH)/water (4/2/1) were added in that order, followed by heating andstirring for about 5 hours at about 80° C. After cooling to roomtemperature, the reaction product was extracted with toluene. An aqueouslayer was removed, and an organic layer was washed with a salinesolution and dried with MgSO₄. MgSO₄ was separated, and the organiclayer was concentrated. Then, the crude product thus obtained wasseparated by silica gel column chromatography (using a mixture solventof hexane and toluene as a developer) to obtain Compound A57 (9.34 g,yield 87%) as a white solid compound. A molecular ion peak of m/z=675was observed by measuring FAB-MS, and from the result, the product wasidentified as Compound A57.

(4) Synthesis of Compound A59

A condensed cyclic compound according to an embodiment, Compound A59,may be synthesized, for example, by the following Reaction 4:

<Synthesis of Intermediate IM-5>

Under an argon atmosphere, to a 500 ml, three neck flask, 10.00 g (48.5mmol) of Intermediate IM-2, 0.84 g (0.03 equiv, 1.5 mmol) of Pd(dba)₂,11.65 g (2.5 equiv, 121.2 mmol) of NaOtBu, 242 ml of toluene, 15.54 g (1equiv, 48.5 mmol) of 2,3-dibromo-6-chloronaphthalene and 0.98 g (0.1equiv, 4.8 mmol) of tBu3P were added in that order, followed by heating,stirring and refluxing for about 6 hours. After cooling to roomtemperature, water was added to the reaction product, and an organiclayer was separately taken. To an aqueous layer, toluene was added, andan organic layer was extracted once more. The organic layer thuscollected was washed with a saline solution and dried with MgSO₄. MgSO₄was separated, and the organic layer was concentrated. Then, the crudeproduct thus obtained was separated by silica gel column chromatography(using a mixture solvent of hexane and toluene as a developer) to obtainIntermediate IM-5 (11.50 g, yield 65%) as a white solid compound. Amolecular ion peak of m/z=364 was observed by measuring FAB-MS, and fromthe result, the product was identified as Intermediate IM-5.

<Synthesis of Compound A59>

Under an argon atmosphere, to a 500 ml, three neck flask, 5.00 g (13.7mmol) of Intermediate IM-5, 0.24 g (0.03 equiv, 0.4 mmol) of Pd(dba)₂,2.63 g (2 equiv, 27.4 mmol) of NaOtBu, 69 ml of toluene, 6.05 g (1.1equiv, 15.1 mmol) ofN-[4-(1-naphthalenyl)phenyl]-4-dibenzothiophenyl-4-amine and 0.28 g (0.1equiv, 1.4 mmol) of tBu3P were added in that order, followed by heating,stirring and refluxing for about 6 hours. After cooling in the air toroom temperature, water was added to the reaction product, and anorganic layer was separately taken. To an aqueous layer, toluene wasadded, and an organic layer was extracted once more. The organic layerthus collected was washed with a saline solution and dried with MgSO₄.MgSO₄ was separated, and the organic layer was concentrated and then,the crude product thus obtained was separated by silica gel columnchromatography (using a mixture solvent of hexane and toluene as adeveloper) to obtain Compound A59 (7.90 g, yield 79%) as a white solidcompound. A molecular ion peak of m/z=729 was observed by measuringFAB-MS, and from the result, the product was identified as Compound A59.

(5) Synthesis of Compound B40

A condensed cyclic compound according to an embodiment, Compound B40,may be synthesized, for example, by the following Reaction 5:

<Synthesis of Intermediate IM-6>

Under an argon atmosphere, to a 500 ml, three neck flask, 20.00 g (170.7mmol) of indole, 7.67 g (0.1 equiv, 34.1 mmol) of Pd(OAc)₂, 94.38 g (2equiv, 682.9 mmol) of K₂CO₃, 58.07 g (1.2 equiv, 204.9 mmol) of5-chloro-2-iodo-1-nitrobenzene and 341 ml of 1,4-dioxane were added inthat order, followed by heating, stirring and refluxing for about 24hours. After cooling to room temperature, the reaction product wasfiltered with celite to separate insoluble residue, water was added tothe remaining reaction product, and an organic layer was separatelytaken. To an aqueous layer, toluene was added, and an organic layer wasextracted once more. The organic layer thus collected was washed with asaline solution and dried with MgSO₄. MgSO₄ was separated, and theorganic layer was concentrated and then, the crude product thus obtainedwas separated by silica gel column chromatography (using a mixturesolvent of hexane and toluene as a developer) to obtain IntermediateIM-6 (18.62 g, yield 40%) as a white solid compound. A molecular ionpeak of m/z=272 was observed by measuring FAB-MS, and from the result,the product was identified as Intermediate IM-6.

<Synthesis of Intermediate IM-7>

Under an argon atmosphere, to a 300 ml, three-neck flask, 15.00 g (55.0mmol) of Intermediate IM-6, 110 ml of o-dichlorobenzene and 36.56 g (4equiv, 220.0 mmol) of P(OEt)₃ were added in that order, followed byheating and stirring at about 160° C. for about 24 hours. After coolingto room temperature, the reaction solvents were distilled off, and thecrude product thus obtained was separated by silica gel columnchromatography (using a mixture solvent of hexane and toluene as adeveloper) to obtain Intermediate IM-7 (10.06 g, yield 76%) as a whitesolid compound. A molecular ion peak of m/z=240 was observed bymeasuring FAB-MS, and from the result, the product was identified asIntermediate IM-7.

<Synthesis of Intermediate IM-8>

Under an argon atmosphere, to a 500 ml, three neck flask, 10.00 g (41.5mmol) of Intermediate IM-7, 0.72 g (0.03 equiv, 1.2 mmol) of Pd(dba)₂,9.98 g (2.5 equiv, 103.9 mmol) of NaOtBu, 208 ml of toluene, 9.80 g (1equiv, 41.5 mmol) of 1,2-dibromobenzene and 0.84 g (0.1 equiv, 4.2 mmol)of tBu3P were added in that order, followed by heating, stirring andrefluxing for about 6 hours. After cooling to room temperature, waterwas added to the reaction product, and an organic layer was separatelytaken. To an aqueous layer, toluene was added, and an organic layer wasextracted once more. The organic layer thus collected was washed with asaline solution and dried with MgSO₄. MgSO₄ was separated, and theorganic layer was concentrated and then, the crude product thus obtainedwas separated by silica gel column chromatography (using a mixturesolvent of hexane and toluene as a developer) to obtain IntermediateIM-8 (10.07 g, yield 77%) as a white solid compound. A molecular ionpeak of m/z=314 was observed by measuring FAB-MS, and from the result,the product was identified as Intermediate IM-8.

<Synthesis of Compound B40>

Under an argon atmosphere, to a 500 ml, three neck flask, 5.00 g (15.9mmol) of Intermediate IM-8, 0.27 g (0.03 equiv, 0.5 mmol) of Pd(dba)₂,3.05 g (2 equiv, 31.8 mmol) of NaOtBu, 80 ml of toluene, 6.10 g (1.1equiv, 17.5 mmol) of N,N-bis(3-dibenzofuranyl)-amine and 0.32 g (0.1equiv, 1.6 mmol) of tBu3P were added in that order, followed by heating,stirring and refluxing for about 6 hours. After cooling to roomtemperature, water was added to the reaction product, and an organiclayer was separately taken. To an aqueous layer, toluene was added, andan organic layer was extracted once more. The organic layer thuscollected was washed with a saline solution and dried with MgSO₄. MgSO₄was separated, and the organic layer was concentrated and then, thecrude product thus obtained was separated by silica gel columnchromatography (using a mixture solvent of hexane and toluene as adeveloper) to obtain Compound B40 (7.08 g, yield 71%) as a white solidcompound. A molecular ion peak of m/z=627 was observed by measuringFAB-MS, and from the result, the product was identified as Compound B40.

(6) Synthesis of Compound B53

A condensed cyclic compound according to an embodiment, Compound B53,may be synthesized, for example, by the following Reaction 6:

<Synthesis of Intermediate IM-9>

Under an argon atmosphere, to a 500 ml, three neck flask, 20.00 g (170.7mmol) of indole, 7.67 g (0.1 equiv, 34.1 mmol) of Pd(OAc)₂, 94.38 g (2equiv, 682.9 mmol) of K₂CO₃, 58.07 g (1.2 equiv, 204.9 mmol) of4-chloro-2-iodo-1-nitrobenzene and 341 ml of 1,4-dioxane were added inthat order, followed by heating, stirring and refluxing for about 24hours. After cooling to room temperature, the reaction product wasfiltered with celite to separate insoluble residue, water was added tothe remaining reaction product, and an organic layer was separatelytaken. To an aqueous layer, toluene was added, and an organic layer wasextracted once more. The organic layer thus collected was washed with asaline solution and dried with MgSO₄. MgSO₄ was separated, and theorganic layer was concentrated, and then, the crude product thusobtained was separated by silica gel column chromatography (using amixture solvent of hexane and toluene as a developer) to obtainIntermediate IM-9 (20.95 g, yield 45%) as a white solid compound. Amolecular ion peak of m/z=272 was observed by measuring FAB-MS, and fromthe result, the product was identified as Intermediate IM-9.

<Synthesis of Intermediate IM-10>

Under an argon atmosphere, to a 300 ml, three-neck flask, 15.00 g (55.0mmol) of Intermediate IM-9, 110 ml of o-dichlorobenzene and 36.56 g (4equiv, 220.0 mmol) of P(OEt)₃ were added in that order, followed byheating and stirring at about 160° C. for about 24 hours. After coolingto room temperature, the reaction solvents were distilled off, and thecrude product thus obtained was separated by silica gel columnchromatography (using a mixture solvent of hexane and toluene as adeveloper) to obtain Intermediate IM-10 (10.99 g, yield 83%) as a whitesolid compound. A molecular ion peak of m/z=240 was observed bymeasuring FAB-MS, and from the result, the product was identified asIntermediate IM-10.

<Synthesis of Intermediate IM-11>

Under an argon atmosphere, to a 500 ml, three neck flask, 10.00 g (41.5mmol) of Intermediate IM-10, 0.72 g (0.03 equiv, 1.2 mmol) of Pd(dba)₂,9.98 g (2.5 equiv, 103.9 mmol) of NaOtBu, 208 ml of toluene, 9.80 g (1equiv, 41.5 mmol) of 1,2-dibromobenzene and 0.84 g (0.1 equiv, 4.2 mmol)of tBu3P were added in that order, followed by heating, stirring andrefluxing for about 6 hours. After cooling to room temperature, waterwas added to the reaction product, and an organic layer was separatelytaken. To an aqueous layer, toluene was added, and an organic layer wasextracted once more. The organic layer thus collected was washed with asaline solution and dried with MgSO₄. MgSO₄ was separated, and theorganic layer was concentrated, and then, the crude product thusobtained was separated by silica gel column chromatography (using amixture solvent of hexane and toluene as a developer) to obtainIntermediate IM-11 (9.81 g, yield 75%) as a white solid compound. Amolecular ion peak of m/z=314 was observed by measuring FAB-MS, and fromthe result, the product was identified as Intermediate IM-11.

<Synthesis of Compound B53>

Under an argon atmosphere, to a 300 ml, three neck flask, 5.00 g (15.9mmol) of Intermediate IM-11, 0.27 g (0.03 equiv, 0.5 mmol) of Pd(dba)₂,3.05 g (2 equiv, 31.8 mmol) of NaOtBu, 80 ml of toluene, 7.16 g (1.1equiv, 17.5 mmol) of N-(9,9-diphenyl-9H-fluoren-2-yl)aniline and 0.32 g(0.1 equiv, 1.6 mmol) of tBu3P were added in that order, followed byheating, stirring and refluxing for about 6 hours. After cooling to roomtemperature, water was added to the reaction product, and an organiclayer was separately taken. To an aqueous layer, toluene was added, andan organic layer was extracted once more. The organic layer thuscollected was washed with a saline solution and dried with MgSO₄. MgSO₄was separated, and the organic layer was concentrated and then, thecrude product thus obtained was separated by silica gel columnchromatography (using a mixture solvent of hexane and toluene as adeveloper) to obtain Compound B53 (9.51 g, yield 87%) as a white solidcompound. A molecular ion peak of m/z=687 was observed by measuringFAB-MS, and from the result, the product was identified as Compound B53.

2. Manufacture and Evaluation of Organic Electroluminescence DeviceIncluding Condensed Cyclic Compound (Manufacture of OrganicElectroluminescence Device)

Organic electroluminescence devices of exemplary embodiments includingthe condensed cyclic compounds of exemplary embodiments in a holetransport layer were manufactured by the method below. Organicelectroluminescence devices of Examples 1 to 6 were manufactured usingthe condensed cyclic compound of Compounds A8, A48, A57, A59, B40 andB53 as materials for a hole transport layer. Organic electroluminescencedevices of Comparative Examples 1 to 4 were manufactured usingComparative Compounds C1 to C4 as materials for a hole transport layer.

The compounds used for forming the hole transport layer in Examples 1 to6 and Comparative Examples 1 to 4 are listed in Table 1.

TABLE 1

Compound A8

Compound A48

Compound A57

Compound A59

Compound B40

Compound B53

Comparative Compound C1

Comparative Compound C2

Comparative Compound C3

Comparative Compound C4

On a glass substrate, ITO was patterned to a thickness of about 1,500 Åand washed with ultra-pure water, and a UV ozone treatment was conductedfor about 10 minutes. Then, a hole injection layer was formed using2-TNANA to a thickness of about 600 Å. A hole transport layer was formedusing the example compound or the comparative compound to a thickness ofabout 300 Å.

Then, an emission layer was formed using ADN doped with 3% TBP to athickness of about 250 Å. Then, an electron transport layer was formedby depositing Alq3 to a thickness of about 250 Å and an electroninjection layer was formed by depositing LiF to a thickness of about 10Å.

Then, a second electrode was formed using Al to a thickness of about1,000 Å.

In an embodiment, a hole injection layer, a hole transport layer, anemission layer, an electron transport layer, an electron injection layerand a second electrode were formed by using a vacuum depositionapparatus.

(Evaluation of Properties of Organic Electroluminescence Device)

The evaluation results of the organic electroluminescence devicesaccording to Example 1 to Example 6, and Comparative Example 1 toComparative Example 4 are shown in Table 2. In Table 2, a device drivingvoltage, a device efficiency and device life for the organicelectroluminescence devices thus manufactured are compared and shown. Inthe evaluation results of the properties of the examples and thecomparative examples in Table 2, the device efficiency represents acurrent efficiency value with respect to a current density of 10 mA/cm²,and the device life represents half life showing the decreasing time ofluminance from an initial luminance of 1,000 cd/m² to half.

The current density, driving voltage and emission efficiency of theorganic electroluminescence devices of the examples and the comparativeexamples were measured using Source Meter (Keithley Instrument Co., 2400series), Luminance Color Meter CS-200 (Konica Minolta Co.), and aprogram for measurement, LabVIEW 8.2 in a dark room.

TABLE 2 Device Driving manufacturing Hole transport voltage EfficiencyDevice life example material (V) (cd/A) LT50 (h) Example 1 Compound A85.7 8.1 2000 Example 2 Compound A48 5.8 7.7 2200 Example 3 Compound A575.6 7.6 2250 Example 4 Compound A59 5.7 7.6 2200 Example 5 Compound B405.6 7.9 2050 Example 6 Compound B53 5.8 7.8 2250 Comparative ComparativeExample 1 Compound Cl 6.0 6.2 1500 Comparative Comparative 6.0 6.2 1450Example 2 Compound C2 Comparative Comparative 5.9 6.0 1500 Example 3Compound C3 Comparative Comparative 5.9 6.0 1400 Example 4 Compound C4

Referring to the results of Table 2, it may be found that the examplesof the organic electroluminescence devices using the condensed cycliccompounds of exemplary embodiments of the inventive step as holetransport materials showed low driving voltage, excellent device lifecharacteristics and excellent device efficiency when compared to thoseof the comparative examples using the comparative compounds in a holetransport layer. The condensed cyclic compound of an embodimentaccording to the inventive concept is an amine compound having apyrrolopyrole skeleton

in a core part, and may show low driving voltage and light-emittingdevice characteristics of long life and high efficiency.

Particularly, the condensed cyclic compounds suggested in exemplaryembodiments disclose an amine compound having indoloindole in a corepart and thus, were found to show lower driving voltage, longer life andhigher efficiency when compared with the comparative examples.

That is, in an embodiment using the condensed cyclic compound of anembodiment as a hole transport material, by introducing a condensed corepart of an amine group having life improving effect and indole or thederivatives thereof, which have excellent heat and charge tolerance, orby introducing a core part having a pyrrolopyrole skeleton, devicecharacteristics were improved further by the amine group and long lifewas achieved.

In the condensed cyclic compound of an embodiment, a nitrogen atomincluded in a core part having a pyrrolopyrrole skeleton improves holetransport capability of a whole compound to improve the recombinationprobability of holes and electrons in an emission layer of an organicelectroluminescence device and improve emission efficiency of thedevice.

In Example 1, since Compound A8 had a folded structure of a condensedindoloindole ring toward a nitrogen atom, high device efficiency wasshown. This was because, the degree of symmetry in a whole molecule wascollapsed in the condensed cyclic compound of Compound A8 and thus,crystallization was restrained and hole transport properties wereimproved, thereby improving the recombination probability of holes andelectrons in an emission layer.

In Examples 2 to 4 including Example Compounds A48, A57 and A59,respectively, the amine group of the example compounds was substitutedfor an aryl ring in which two nitrogen atoms having plentiful electronswere substituted, and in Example Compound B53, an amine group and anitrogen atom were positioned in para-position, and Examples 2 to 4 andExample 6 showed markedly improved device life. This was because orbitalin a HOMO state was sufficiently expanded and stability in a radicalstate was improved.

In addition, in Example 5 including an amine-substituted condensedcyclic compound such as Example Compound B40, device efficiency anddevice life kept balance and both were favorably improved.

The Comparative Compounds of Comparative Examples 1 to 3 were aminecompounds having a condensed cyclic nitrogen-containing heterocycle in acore part, but the number of nitrogen atoms included in the heterocyclewas different from that of the examples. Thus, low efficiency was shownwhen compared with the examples. This was thought that carrier balancewas collapsed in the comparative compounds, and the nitrogen atomsincluded in the condensed heterocycle largely contributed to theimprovement of hole transport properties.

Since Comparative Example 4 used an amine compound including anindoloindole skeleton but did not include a rigid condensed cyclic core,it was liable to arise decomposition under high temperature conditionsand attained short device life when compared with the examples. Inaddition, since a phenyl group bonded to a nitrogen atom was orthogonal,distance between molecules increased, the propagation of holesdecreased, and low device efficiency was shown when compared with theexamples.

Referring to the results of Table 2, if the condensed cyclic compound ofan embodiment of the inventive concept was included in a hole transportlayer, longer life and higher efficiency were found when compared with acase where the comparative compound was included in the hole transportlayer. That is, the condensed cyclic compound of an embodiment was anamine compound including a pyrrolopyrole skeleton in a core part whichwas a condensed ring part, and kept the properties of the amine compoundwhich exhibited hole transport properties, improved the electrontolerance of a material due to the condensed ring part and layer qualityand thermal stability, and achieved both high emission efficiency andlong life.

In addition, the organic electroluminescence device of an embodimentincluded the condensed cyclic compound of an embodiment in at least oneorganic layer which was disposed between a first electrode and a secondelectrode, or particularly in a hole transport region, and might achieveimproved device efficiency and long life.

The organic electroluminescence device of an embodiment may showimproved device properties with a low driving voltage, long life andhigh efficiency.

The condensed cyclic compound of an embodiment may be applied in thehole transport region of an organic electroluminescence device andcontribute to the long life and high efficiency of the organicelectroluminescence device.

Although the exemplary embodiments of the present invention have beendescribed, it is understood that the present invention should not belimited to these exemplary embodiments but various changes andmodifications can be made by one ordinary skilled in the art within thespirit and scope of the present invention as hereinafter claimed.

What is claimed is:
 1. An organic electroluminescence device,comprising: a first electrode; a second electrode disposed on the firstelectrode; and a plurality of organic layers disposed between the firstelectrode and the second electrode, wherein at least one organic layeramong the plurality of organic layers comprises a condensed cycliccompound represented by the following Formula 1:

in Formula 1, each of Ar1, Ar2, and Ar3 is independently a substitutedor unsubstituted aryl group having 6 to 40 carbon atoms for forming aring, or a substituted or unsubstituted heteroaryl group having 2 to 40carbon atoms for forming a ring, excluding a case where one or both ofAr2 or Ar3 is a substituted or unsubstituted carbazole group, each ofX1, X2, and X3 is independently *-L-NR₁R₂, one of a1, a2, and a3 is 1and the others are 0, L is a direct linkage, a substituted orunsubstituted arylene group having 6 to 30 carbon atoms for forming aring, or a substituted or unsubstituted heteroarylene group having 2 to30 carbon atoms for forming a ring, and each of R₁ and R₂ isindependently a substituted or unsubstituted alkyl group having 1 to 20carbon atoms, a substituted or unsubstituted aryl group having 6 to 40carbon atoms for forming a ring, or a substituted or unsubstitutedheteroaryl group having 2 to 40 carbon atoms for forming a ring, orcombined with each other to form a ring.
 2. The organicelectroluminescence device of claim 1, wherein the plurality of organiclayers comprise: an emission layer; and a hole transport region disposedbetween the first electrode and the emission layer, wherein the holetransport region comprises the condensed cyclic compound represented byFormula
 1. 3. The organic electroluminescence device of claim 2, whereinthe emission layer emits blue light.
 4. The organic electroluminescencedevice of claim 2, wherein the emission layer comprises at least one ofanthracene derivatives, pyrene derivatives, fluoranthene derivatives,chrysene derivatives, dihydro benzanthracene derivatives, ortriphenylene derivatives.
 5. The organic electroluminescence device ofclaim 1, wherein Formula 1 is represented by the following Formula 1-1or Formula 1-2:

in Formula 1-1 and Formula 1-2, Ar1, Ar2, Ar3, L, R₁ and R₂ are the sameas defined in Formula
 1. 6. The organic electroluminescence device ofclaim 1, wherein Ar1 is a substituted or unsubstituted benzene ring, ora substituted or unsubstituted naphthalene ring.
 7. The organicelectroluminescence device of claim 1, wherein each of Ar2 and Ar3 isindependently a substituted or unsubstituted benzene ring, a substitutedor unsubstituted naphthalene ring, a substituted or unsubstitutedphenanthrene ring, a substituted or unsubstituted benzofuran ring, asubstituted or unsubstituted dibenzofuran ring, a substituted orunsubstituted benzothiophene ring, a substituted or unsubstituteddibenzothiophene ring, a substituted or unsubstituted pyridine ring, ora substituted or unsubstituted quinoline ring.
 8. The organicelectroluminescence device of claim 1, wherein Ar2 and Ar3 are the same.9. The organic electroluminescence device of claim 1, wherein each ofAr2 and Ar3 is independently represented by any one of the followingAr-a to Ar-i:

in Ar-a to Ar-i, each of R₁₁ to R₁₉ is independently a hydrogen atom, adeuterium atom, a halogen atom, a substituted or unsubstituted silylgroup, a substituted or unsubstituted alkyl group having 1 to 10 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30 carbonatoms for forming a ring, or a substituted or unsubstituted heteroarylgroup having 2 to 30 carbon atoms for forming a ring, or combined withan adjacent group to form a ring, each of a11 to a19 is independently aninteger of 0 to 4, and dotted lines represent combined parts forming acondensed ring.
 10. The organic electroluminescence device of claim 1,wherein Formula 1 is represented by the following Formula 2-1 or Formula2-2:

in Formula 2-1 and Formula 2-2, each of R₃ and R₄ is independently ahydrogen atom, a deuterium atom, a halogen atom, a substituted orunsubstituted silyl group, a substituted or unsubstituted alkyl grouphaving 1 to 10 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms for forming a ring, or a substituted orunsubstituted heteroaryl group having 2 to 30 carbon atoms for forming aring, or combined with an adjacent group to form a ring, “y” and “z” areeach independently an integer of 0 to 3, and X1 to X3, and a1 to a3 arethe same as defined in Formula
 1. 11. The organic electroluminescencedevice of claim 1, wherein at least one organic layer comprises at leastone of compounds represented in the following Compound Group 1 andCompound Group 2:


12. A condensed cyclic compound represented by the following Formula 1:

in Formula 1, each of Ar1, Ar2, and Ar3 is independently a substitutedor unsubstituted aryl group having 6 to 40 carbon atoms for forming aring, or a substituted or unsubstituted heteroaryl group having 2 to 40carbon atoms for forming a ring, excluding a case where one or both ofAr2 and Ar3 is a substituted or unsubstituted carbazole group, each ofX1, X2, and X3 is independently *-L-NR₁R₂, any one of a1, a2, and a3 is1, and the others are 0, L is a direct linkage, a substituted orunsubstituted arylene group having 6 to 30 carbon atoms for forming aring, or a substituted or unsubstituted heteroarylene group having 2 to30 carbon atoms for forming a ring, and Each of R₁ and R₂ isindependently a substituted or unsubstituted alkyl group having 1 to 20carbon atoms, a substituted or unsubstituted aryl group having 6 to 40carbon atoms for forming a ring, or a substituted or unsubstitutedheteroaryl group having 2 to 40 carbon atoms for forming a ring, orcombined with each other to form a ring.
 13. The condensed cycliccompound of claim 12, wherein Formula 1 is represented by the followingFormula 1-1 or Formula 1-2:

in Formula 1-1 and Formula 1-2, Ar1 to Ar3, L, R₁ and R₂ are the same asdefined in Formula
 1. 14. The condensed cyclic compound of claim 12,wherein Ar1 is a substituted or unsubstituted benzene ring, or asubstituted or unsubstituted naphthalene ring.
 15. The condensed cycliccompound of claim 12, wherein each of Ar2 and Ar3 is independently asubstituted or unsubstituted benzene ring, a substituted orunsubstituted naphthalene ring, a substituted or unsubstitutedphenanthrene ring, a substituted or unsubstituted benzofuran ring, asubstituted or unsubstituted dibenzofuran ring, a substituted orunsubstituted benzothiophene ring, a substituted or unsubstituteddibenzothiophene ring, a substituted or unsubstituted pyridine ring, ora substituted or unsubstituted quinoline ring.
 16. The condensed cycliccompound of claim 12, wherein Ar2 and Ar3 are the same.
 17. Thecondensed cyclic compound of claim 12, wherein each of Ar2 and Ar3 isindependently represented by any one of the following Ar-a to Ar-i:

in Ar-a to Ar-i, each of R₁₁ to R₁₉ is independently a hydrogen atom, adeuterium atom, a halogen atom, a substituted or unsubstituted silylgroup, a substituted or unsubstituted alkyl group having 1 to 10 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30 carbonatoms for forming a ring, or a substituted or unsubstituted heteroarylgroup having 2 to 30 carbon atoms for forming a ring, or combined withan adjacent group to form a ring, each of all to a19 is independently aninteger of 0 to 4, and dotted lines represent combined parts forming acondensed ring.
 18. The condensed cyclic compound of claim 12, whereinFormula 1 is represented by the following Formula 2-1 or Formula 2-2:

in Formula 2-1 and Formula 2-2, each of R₃ and R₄ is independently ahydrogen atom, a deuterium atom, a halogen atom, a substituted orunsubstituted silyl group, a substituted or unsubstituted alkyl grouphaving 1 to 10 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms for forming a ring, or a substituted orunsubstituted heteroaryl group having 2 to 30 carbon atoms for forming aring, or combined with an adjacent group to form a ring, each of “y” and“z” is independently an integer of 0 to 3, and X1, X2, X3, a1, a2, anda3 are the same as defined in Formula
 1. 19. The condensed cycliccompound of claim 12, wherein L is a direct linkage or represented byany one of the following L1, L2, L3, and L4:


20. The condensed cyclic compound of claim 12, wherein the condensedcyclic compound represented by Formula 1 is any one of the compoundsrepresented in the following Compound Group 1 and Compound Group 2: